Updates: “Way Too Selective?” Responds

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It’s time again for “Dear Wendy Updates,” a feature where people I’ve given advice to in the past let us know whether they followed the advice and how they’re doing today. After the jump, we hear from “Way Too Selective?” who was asked by a guy she went out with a few times (and slept with on their second date) whether she had slept with anyone else the night before she slept with him. “I laughed,” she wrote, “made some joke about the question, and said no. Then (and I should have seen this coming), he told me that he had hooked up with someone the same weekend we hooked up, and ‘wanted to be honest about it so I wouldn’t be hurt,’ and also said he was asking to ‘see how I would respond.'” Not liking being tested like that, she wondered if his behavior was a red flag. After the jump, find out whether she stuck things out with him or MOAd before he got weirder.

In May I wrote in about a guy I’d just started dating who caught me off guard with an over-share of his concurrent sex life in order to judge my response. I want to thank the readers for their comments, and you for taking the time to answer my letter on your site. It was great to hear that I wasn’t being way too analytical or just finding an excuse to bail, but that most agreed his behavior actually was awkward, manipulative, and unappealing. I also appreciated the comments suggesting I was engaging in high-risk (or skanky?) sexual behavior by sleeping with him so early on. I can assure you all that I contracted neither STDs nor emotional damage in my adventures! We hung out one more time after the awkwardness and although, Wendy, I loved your suggested response, I decided to just be sincere with him, since I do believe he has no idea what he’s doing in dating, and that it might be a favor to the next girl if I explained what went wrong. I told him that it will always come across better to just ask respectufully what you want to know, say what you want to say, and drop the mind games. I told him that if you want to get to know someone, it’s better to just take the time, pay attention, and be honest about yourself and what you are looking for. Injecting weird ‘challenges’ into the mix is only going to ensure you lose your chance with a lot of great girls. He said, Thanks, and I said Best of Luck, and we parted ways, and we’ve been off each other’s radar since.

Again, thank you for the thoughtful and funny advice, and thanks to all the commenters for their insight and good humor.

Sounds like all’s well that ends well then, right? Thanks for the update and good luck in the future!

If you’re someone I’ve given advice to in the past, I’d love to hear from you, too. Email me at [email protected] with a link to the original post, and let me know whether you followed the advice and how you’re doing now.